(3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

Base Information

• Chemical Name: (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide
• CAS No.: 1351186-41-8
• Molecular Formula: C₃₉H₅₂N₂O₂S
• Molecular Weight: 612.92
• Mol file: 1351186-41-8.mol

Synonyms:(3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

Chemical Property of (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide

There total 18 articles about (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

(R)-1-(tritylthio)but-3-en-2-amine (1351186-44-1) + (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyloctanoic acid (1351186-40-7) → (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-41-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jo201951s

Reference yield:

(R)-N,2-dimethyl-N-((S)-5-methyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)oct-6-en-1-yl)butanamide → (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-41-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(I) bromide dimethylsulfide complex / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

1.2: -78 - -40 °C / Inert atmosphere

2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 12 h / 20 °C

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With dmap; copper(I) bromide dimethylsulfide complex; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo201951s

Reference yield:

C25H38N2O4 → (3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyl-N-((R)-1-(tritylthio)but-3-en-2-yl)octanamide (1351186-41-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 12 h / 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 20 °C / Inert atmosphere

With dmap; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo201951s

upstream raw materials:

(R)-N-((S)-6-(tert-butyldiphenylsilyloxy)-5-methylhexyl)-N,2-dimethylbutanamide

(R)-N-((S)-6-hydroxy-5-methylhexyl)-N,2-dimethylbutanamide

(R)-1-(tritylthio)but-3-en-2-amine

(3R,4S)-8-((R)-N,2-dimethylbutanamido)-3,4-dimethyloctanoic acid